American Airlines, United, and Southwest have round-trip flights from Denver (DEN) to Grand Cayman (GCM) for $317-$338 with a connection. Flights February to May. Origin/Destination reversible.
Category: <span>Grand Cayman</span>
JetBlue has round-trip flights from Atlanta (ATL) to Grand Cayman (GCM) for $241-$289 with a connection. Flights January to June. Departures on Tuesday, Thursday, and Saturday. Origin/Destination reversible.
Expedia will often have a discount for jetBlue fares if you are logged into their website, in this case, for me, it was about $7 dollars, but it varies. (see screenshot for an example)
The upgrade from “Blue Basic” to “Blue” is $37.
JetBlue has round-trip flights from Atlanta (ATL) to Grand Cayman (GCM) for $239-$288 with a connection. Flights December to May. Departures on Tuesday, Thursday, and Saturday. Origin/Destination reversible. No Christmas dates available.
JetBlue has posted some round-trip flights from Atlanta (ATL) to Grand Cayman (GCM) for $311-$370 with a connection. Flights December to May. Departures on Tuesday, Thursday, and Saturday. Origin/Destination reversible. No Christmas dates available.
JetBlue has round-trip flights from New York (JFK) to Grand Cayman (GCM) for $256-$279, NONSTOP. Flights November to March. Weekends available. Origin/Destination reversible. Dates over Thanksgiving are available.
United and American Airlines have round-trip flights from Denver (DEN) to Grand Cayman (GCM) for $382-$390 with a connection. Flights November to December. Very few weekends available. Origin/Destination reversible. Holiday blackouts.
United and American Airlines have round-trip flights from Denver (DEN) to Grand Cayman (GCM) for $382-$390 with a connection. Flights November to December. Origin/Destination reversible. Holiday blackouts.
American Airlines has round-trip flights from Atlanta (ATL) to Grand Cayman (GCM) for $362-$371 with a connection. Flights in August, October, November, December, and January. Departures on Monday, Tuesday, Wednesday, and Sunday. Origin/Destination reversible. Holiday blackouts.
JetBlue has round-trip flights from New York (JFK) to Grand Cayman (GCM) for $246, NONSTOP. Flights February to April. Very few weekends available.
JetBlue’s “Basic” fares allow for a carry-on bag and a small personal item (17 x 13 x 8 inches), like a Jansport SuperBreak backpack without a fee. You can avoid seat selection fees by accepting the randomly assigned seat at the gate.
JetBlue has round-trip flights from Seattle (SEA) to Grand Cayman (GCM) for $433-$448 with a connection. Flights November to December. Departures on Friday and Sunday. Very few weekends available. Origin/Destination reversible. Holiday blackouts.
Flight is an overnight “Red-Eye”.
JetBlue and Delta have round-trip flights from Denver (DEN) to Grand Cayman or Saint Lucia (GCM) for $377-$441 with a connection. Grand Cayman flights August to May. Saint Lucia flights September to April. Departures on Monday, Tuesday, Wednesday, Saturday, and Sunday. Extended weekends available. Origin/Destination reversible.
JetBlue’s “Basic” fares only allow a small personal item (17 x 13 x 8 inches), like a Jansport SuperBreak backpack without a fee. A regular sized carry-on bag will incur a bag fee. To avoid bag fees, consider using a credit card with the “first free checked bag” perk.
JetBlue has round-trip flights from Phoenix (PHX) to Grand Cayman (GCM) for $357 with a connection. Flights in August. Departures on Monday, Tuesday, Wednesday, Thursday, and Sunday. No Fridays or Saturdays. Very few extended weekends available. Origin/Destination reversible.
JetBlue’s “Basic” fares only allow a small personal item (17 x 13 x 8 inches), like a Jansport SuperBreak backpack without a fee. A regular sized carry-on bag will incur a bag fee. To avoid bag fees, consider using a credit card with the “first free checked bag” perk.
American Airlines has round-trip flights from New York/Newark (LGA/EWR) to Grand Cayman (GCM) for $231-$238 with a connection. Flights July to April. Weekends available. Origin/Destination reversible.
A Carry-on bag and also a personal item is allowed for free on American. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.
Delta has round-trip flights from Chicago (ORD/MDW) to Grand Cayman (GCM) for $255 with a connection. Flights in March. No Saturday departures. Very few weekends available. Origin/Destination reversible.
A Carry-on bag and also a personal item is allowed for free on Delta. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.
JetBlue has round-trip flights from New York (JFK) to Grand Cayman, Belize, Costa Rica, Curacao, or Guatemala City (GCM, BZE, LIR, CUR, GUA) for $227-$349, NONSTOP. Flights February to May. No last minute fares available. Origin/Destination reversible.
JetBlue’s “Basic” fares only allow a small personal item (17 x 13 x 8 inches), like a Jansport SuperBreak backpack without a fee. A regular sized carry-on bag will incur a bag fee. To avoid bag fees, consider using a credit card with the “first free checked bag” perk.
American Airlines has round-trip flights from Chicago (ORD) to Grand Cayman (GCM) for $326-$333 with a connection. Flights January to May. Departures on Tuesday and Wednesday. Origin/Destination reversible.
Hopper has a Cyber Monday coupon for -$200 off Cayman Hotels.
A Carry-on bag and also a personal item is allowed for free on American. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.
Hopper has a $100 off coupon for Cayman Islands.
American Airlines has round-trip flights from Denver (DEN) to Grand Cayman (GCM) for $332-$353 with a connection. If you apply the Hopper coupon, the cost of the round-trip is about $237-$258. Flights August to April. Very few weekends available. Origin/Destination reversible.
A Carry-on bag and also a personal item is allowed for free on American. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.
Most domestic carriers have round-trip flights from Chicago or Milwaukee (ORD, MDW, MKE) to various destinations in Hawaii, the Caribbean, Central America, or Mexico for $177-$408, NONSTOP or with a connection. Dates vary, you’ll need to look at the linked Calendar. Origin/Destination reversible. No Major Holiday dates available. We believe most of these discount fares will end after 06/15/2023.
Noteworthy destinations in this list: San Juan ($177), Belize ($363), Honolulu ($376), Kahului ($376), Costa Rica ($408), and Grand Cayman ($294).
Hopper has a $100 off Cayman Islands coupon.
American Airlines has round-trip flights from Chicago (ORD) to Grand Cayman (GCM) for $286-$289 with a connection. If you apply the Hopper coupon, the cost of the round-trip is about $188. Flights August to December. Departures on Monday, Tuesday, Wednesday, and Sunday. Origin/Destination reversible. No Christmas dates available.
Hopper has a $100 off Cayman Islands coupon.
United has round-trip flights from Chicago (ORD) to Grand Cayman (GCM) for $384, NONSTOP. If you apply the Hopper coupon, the cost of the round-trip is about $284. Flights in October. Departures on Sunday.
This deal is very limited, it’s only available as a round-trip departing Oct 29, returning Nov 04, but at this price I think it is worth it to whomever picks it up.

